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794139

Sigma-Aldrich

5 -Cyclopentadienyl)[N,N-dimethyl-Ν′-(2-pyridinylmethylidene)propane-1,3-diamine]ruthenium hexafluorophosphate

Synonym(s):

Herzon Reductive Hydration Catalyst

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About This Item

Empirical Formula (Hill Notation):
C16H22F6N3PRu
CAS Number:
Molecular Weight:
502.40
UNSPSC Code:
12161600
PubChem Substance ID:
NACRES:
NA.22

form

powder

Quality Level

reaction suitability

core: ruthenium
reagent type: catalyst

mp

>180 °C

SMILES string

CN(C)CCC/N=C/C1=NC=CC=C1.F[P-](F)(F)(F)(F)F.[C]2[C][C][C][C]2.[Ru+]

InChI

1S/C11H17N3.C5H5.F6P.Ru/c1-14(2)9-5-7-12-10-11-6-3-4-8-13-11;1-2-4-5-3-1;1-7(2,3,4,5)6;/h3-4,6,8,10H,5,7,9H2,1-2H3;1-5H;;/q;;-1;+1/b12-10+;;;

InChI key

KUSUXOOKLDLSSI-AKMNYRKMSA-N

General description

5 -Cyclopentadienyl)[N,N-dimethyl-N′-(2-pyridinylmethylidene)propane-1,3-diamine]ruthenium hexafluorophosphate is also referred to as Herzon reductive hydration catalyst. Herzon reductive hydration catalyst is a half-sandwich ruthenium complex. It is a tridentate nitrogen-based ligand containing a hemilabile 3-(dimethylamino)propyl group. It participates in the conversion of terminal alkynes to linear alcohols.

Application

Catalyst mediates the transformation of alkynes to alcohols through an anti-Markovnikov addition. This reaction occurs at room temperature with the use of formic acid to assist in the reduction of the intermediate aldehyde to the corresponding alcohol.

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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Mingshuo Zeng et al.
Journal of the American Chemical Society, 136(19), 7058-7067 (2014-05-03)
The conversion of terminal alkynes to functionalized products by the direct addition of heteroatom-based nucleophiles is an important aim in catalysis. We report the design, synthesis, and mechanistic studies of the half-sandwich ruthenium complex 12, which is a highly active

Related Content

The Herzon group has developed highly active catalysts for the anti-Markovnikov hydration and reductive hydration of terminal alkynes to form aldehydes and linear alcohols, respectively.

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